Literature DB >> 26101939

Homohalocyclization: Electrophilic Bromine-Induced Cyclizations of Cyclopropanes.

Christian Rösner1, Ulrich Hennecke1.   

Abstract

An efficient method for the halocyclization of cyclopropanes has been developed. The cyclopropanes undergo a 1,3-addition reaction to form homohalocyclization products compared to conventional alkene halocyclizations. The reaction can be induced by various electrophilic halogenating agents including 1,3-dibromo-5,5-dimethylhydantoin and N-iodosuccinimide. In cyclopropane derivatives with a preexisting stereocenter, excellent induced diastereoselectivities can be observed.

Entities:  

Year:  2015        PMID: 26101939     DOI: 10.1021/acs.orglett.5b01315

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

1.  Catalytic 1,3-Difunctionalization via Oxidative C-C Bond Activation.

Authors:  Steven M Banik; Katrina M Mennie; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2017-06-29       Impact factor: 15.419

2.  Electrochemical C-C bond cleavage of cyclopropanes towards the synthesis of 1,3-difunctionalized molecules.

Authors:  Pan Peng; Xingxiu Yan; Ke Zhang; Zhao Liu; Li Zeng; Yixuan Chen; Heng Zhang; Aiwen Lei
Journal:  Nat Commun       Date:  2021-05-24       Impact factor: 14.919

3.  Diastereoselective Synthesis of Spirocyclopropanes under Mild Conditions via Formal [2 + 1] Cycloadditions Using 2,3-Dioxo-4-benzylidene-pyrrolidines.

Authors:  Yi Li; Qing-Zhu Li; Li Huang; Hong Liang; Kai-Chuan Yang; Hai-Jun Leng; Yue Liu; Xu-Dong Shen; Xiao-Jun Gou; Jun-Long Li
Journal:  Molecules       Date:  2017-02-22       Impact factor: 4.411

4.  Ring-opening hydroarylation of monosubstituted cyclopropanes enabled by hexafluoroisopropanol.

Authors:  Edward Richmond; Jing Yi; Vuk D Vuković; Fatima Sajadi; Christopher N Rowley; Joseph Moran
Journal:  Chem Sci       Date:  2018-06-28       Impact factor: 9.825

5.  Boron tribromide as a reagent for anti-Markovnikov addition of HBr to cyclopropanes.

Authors:  Matthew H Gieuw; Shuming Chen; Zhihai Ke; K N Houk; Ying-Yeung Yeung
Journal:  Chem Sci       Date:  2020-08-04       Impact factor: 9.825

6.  Complex Carbocyclic Skeletons from Aryl Ketones through a Three-Photon Cascade Reaction.

Authors:  Line Naesborg; Christian Jandl; Andreas Zech; Thorsten Bach
Journal:  Angew Chem Int Ed Engl       Date:  2020-01-30       Impact factor: 15.336

  6 in total

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